84565-94-6Relevant academic research and scientific papers
A case of pictet-spengler revisited: Application to the synthesis of dihydroisocoumarins
Choukchou-Braham,Mostefa-Kara,Cheikh,Didi,Villemin
, p. 169 - 178 (2005)
The reaction of Pictet-Spengler was revisited, and its modified conditions were applied to develop a general methodology toward the synthesis of dihydroisocoumarins containing a no-electron rich aromatic ring.
Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds
Wang, Haining,Dai, Xi-Jie,Li, Chao-Jun
, p. 374 - 378 (2017/04/03)
Nucleophilic addition reactions of organometallic reagents to carbonyl compounds for carbon-carbon bond construction have played a pivotal role in modern chemistry. However, this reaction's reliance on petroleum-derived chemical feedstocks and a stoichiometric quantity of metal have prompted the development of many carbanion equivalents and catalytic metal alternatives. Here, we show that naturally occurring carbonyls can be used as latent alkyl carbanion equivalents for additions to carbonyl compounds, via reductive polarity reversal. Such 'umpolung' reactivity is facilitated by a ruthenium catalyst and diphosphine ligand under mild conditions, delivering synthetically valuable secondary and tertiary alcohols in up to 98% yield. The unique chemoselectivity exhibited by carbonyl-derived carbanion equivalents is demonstrated by their tolerance to protic reaction media and good functional group compatibility. Enantioenriched tertiary alcohols can also be accessed with the aid of chiral ligands, albeit with moderate stereocontrol. Such carbonyl-derived carbanion equivalents are anticipated to find broad utility in chemical bond formation.
ELECTROSYNTHESIS OF ALCOHOLS FROM ORGANIC HALIDES AND KETONES OR ALDEHYDES
Sibille, Soline,d'Incan, Esther,Leport, Louis,Perichon, Jacques
, p. 3129 - 3132 (2007/10/02)
The electrosynthesis of a wide range of alcohols from organic halides and ketones or aldehydes is achieved under simple and mild conditions in an undivided electrolytic cell using different sacrificial anodes.
SOME ORGANIC REACTIONS PROMOTED BY SAMARIUM DIIODIDE
Souppe, J.,Danon, L.,Namy, J.L.,Kagan, H.B.
, p. 227 - 236 (2007/10/02)
Various homoallylic alcohols and homobenzylic alcohols were prepared by the reaction between aldehydes and allylic or benzylic halides in the presence of samarium diiodide.This iodide is also a very good reagent for formation of pinacols from aldehydes or ketones.The reactions are especially fast and selective in the case of substituted benzaldehydes.The reactivities of various nitrogen functional groups (imine, oxime, nitro, azo, cyano) towards SmI2 were also examined.
SAMARIUM DIIODIDE AS COUPLING AGENT BETWEEN ALDEHYDES AND ORGANIC HALIDES FOR THE SYNTHESIS OF HOMOALLYLIC AND HOMOBENZYLIC ALCOHOLS
Souppe, J.,Namy, J. L.,Kagan, H. B.
, p. 3497 - 3500 (2007/10/02)
Many aliphatic aldehydes are transformed into secondary alcohols by reaction with allyl halides or benzylic halides in presence of SmI2
